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Seven Of Our Most And Least Favourite Bosses In Movies

What is a more perfect time to do a quick recap of our most iconic bosses than on Bosses Day (US)?

From “Schindler’s List” to “The Devil Wears Prada”, these seven films feature the employers you love and hate.

Willy Wonka and the Chocolate Factory (1971)

Gene Wilder as Willy Wonka
“Welcome my friends, welcome to my chocolate factory.” – Willy Wonker
This movie is about non-discriminatory hiring practices and atomizes obnoxious disruptive children or drowns them in chocolate. What a yummy death!

Schindler’s List (1993)

Liam Neeson as Oskar Schindler
“Whoever saves one life, saves the world entire.” – Oskar Schindler
A factory owner slowly bankrupts himself to save 600 Jewish workers from extermination during World War II.


The Devil’s Advocate (1997)

John Milton as Al Pacino
“Free will. It’s like butterfly wings: once touched, they never get off the ground. No, I only set the stage. You pull your own strings.” – Al Pacino
Kevin Lomax (Keanu Reeves) starts working at a law firm where his boss, John Milton (Al Pacino), has more than just power of attorney. John first presents himself as a father figure who showers Kevin with praise, advice, and perks, but then is revealed to be no less than Satan himself – with the character employing his power to memorably drive Kevin’s loving wife, Mary Ann (Charlize Theron), completely and utterly insane. The next time you’re complaining about your boss, remember that it could be worse: He or she could be the Devil.

The Devil Wears Prada (2006)

Meryl Streep as Miranda Priestly
“Details of your incompetence do not interest me.” – Miranda Priestly
A prickly and demanding boss terrorises and insults majority of her employees, especially her new assistant, Andy Sachs (Anne Hathaway). And it’s much more than verbal abuse as Miranda sends Andy on impossible missions like booking a flight during a hurricane.


The Proposal (2009)

Sandra Bullock as Margaret Tate
“Do you prefer Margaret or ‘Satan’s Mistress’?” – Grandma Annie, while being introduced to Margaret
An overbearing boss forces her assistant, Andrew Paxton (Ryan Reynolds), to marry her when she learns that she may face deportation to Canada due to an expired visa. That’s a lot of unpaid overtime, madam.

Horrible Bosses (2011)

Jennifer Aniston as Dr. Julia Harris
“You’re a raper, you raped me, that’s a RAPE!” – Dale Arbus
Come on! It’s right in the title. An aggressive dentist has a habit of sexually harassing her assistant Dale Arbus (Charlie Day).

The Wolf Of Wall Street (2013)

Jordan Belfort as Leonardo Dicaprio
“Happy hour is mandatory and awesome.”
Enough said.

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Bosses Day
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